Rajat Gupta: Why, and what's next?

Decades ago, when Rajat Gupta was but an Indian schoolboy, a business professor gave him some sage advice. "I told him once," says Bala Balachandran, "'If you are in a herd of pigs, you'll also smell like a pig.'" Unfortunately, Balachandran's professorial wisdom faded from the disgraced ex-McKinsey managing director's memory as early as 2007, when he left the venerated firm to pursue a second career in high-stakes deal-making. Now, with a civil suit pending against him and his name turning up on a nearly daily basis at the most publicized insider trading trial in history, I think it's safe to say that Gupta wishes he had taken his former mentor's words to heart.

Amongst the hogs

Gupta was already amongst the hogs when he started New Silk Route, a private equity fund, with three shady characters that Bloomberg suggests "had had trouble with regulatory authorities" in the past. Soon after, Raj Rajaratnam plowed $50 million of his own cash into the project. Started in 2006, Gupta's pet money-making project was born before Gupta had even left McKinsey. Bloomberg couldn't help but beg the question "why?"—with the top job at one of the most revered corporations on Earth, Gupta had everything to lose and very little to gain. So why did he leave his company and his industry behind?

Good, old fashioned greed might explain Gupta's predicament. In wiretapped phone calls, Rajaratnam and Anil Kumar appear to subscribe to this possibility. "I think here he sees an opportunity to make $100 million over the next five or 10 years without doing a lot of work," said Rajaratnam of Gupta's private equity ambitions. The pair also suggested that Gupta wanted to run in "a billionaire circle," not the relatively low-brow millionaire circles all three ran in at the time.

Greed isn't only measured by money, of course; Gupta's essentially honorary role on the board at Goldman Sachs (he admitted that he didn't make much money there) suggests that his image as an influential powerbroker was just as important as the thickness of his wallet.

Perhaps greed is too harsh a descriptor to attach to someone who simply lost his way amongst the "pigs". "I think Rajat Gupta got caught in that whole New York milieu where people measure themselves by their net worth, the size of their bonus, or square footage of their house," said Shoba Narayan, the wife of one of Gupta's colleagues, to Bloomberg. "If he’d lived away from that incestuous Wall Street set, perhaps none of this would have happened." Perhaps.

Where to, Rajat?

Regardless of his intentions, "what's next?" might be a better question to pose than "why?"—we'll never know Gupta's reasons for his actions, and he may never know them himself. We can, however, speculate on what the future will hold for the man who fell from such great heights.

Let's start with the obvious: "He’ll never recover the pristine reputation he had before," said a Wall Street analyst to Bloomberg. While there is a civil case pending against Gupta, slated to begin sometime this summer, the worst he could get as a result is a fine and wrist-slap, something his former colleagues at Goldman Sachs will be intimately familiar with. The judge could also ban Gupta from serving on the board of a public company for life, but it was highly unlikely that he ever would have done so anyway. A criminal trial for Gupta—though the evidence seems, well, evident—appears unlikely if the SEC hasn't already filed criminal charges. Like Gupta, McKinsey might never recover the "pristine reputation" of its pre-Gupta (and arguably pre-Enron) days, so it's unlikely that the firm or any of its prestigious rivals would bring him on board. Gupta resigned from the board of New Silk Route, likely closing that self-made door for the future, and he also resigned from the board of the Indian School of Business, another prestigious pet project.

What all of these seemingly dead-end opportunities have in common, though, is that Gupta served each honorably for the majority of his career. One doesn't rise to the top of McKinsey for no reason; same goes for Goldman Sachs, and virtually every other company on Gupta's CV. He still has a lot to offer a corporation that isn't afraid to take a PR hit (or arguably, even one that is).

But maybe he'll prefer to spend the rest of his days sunbathing in the Maldives or kicking it in India. Maybe he'll laugh last after all: if the SEC's allegations are true, is there any question that Gupta would have preferred this public dressing down to a lengthy stint in federal prison?

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